Sciencemadness Discussion Board

tribromoisocyanuric acid (tbica)

Loptr - 10-2-2015 at 06:31

Since there are many available sources of TCICA, does anyone know if there is an easily available source for the brominated form?

http://en.wikipedia.org/wiki/Tribromoisocyanuric_acid


[Edited on 10-2-2015 by Loptr]

woelen - 10-2-2015 at 07:39

This compound is not common and I think you will have a hard time finding a source for this, especially if you want a source, which delivers to private persons.

The bromine variant for swimming pools is 1-Bromo-3-chloro-5,5-dimethylhydantoin (BCDMH). BCDMH can be purchased in many countries and if you cannot find it locally, then you certainly can find it through eBay.

Loptr - 10-2-2015 at 09:54

Quote: Originally posted by woelen  
This compound is not common and I think you will have a hard time finding a source for this, especially if you want a source, which delivers to private persons.

The bromine variant for swimming pools is 1-Bromo-3-chloro-5,5-dimethylhydantoin (BCDMH). BCDMH can be purchased in many countries and if you cannot find it locally, then you certainly can find it through eBay.


Thank you for the response, woelen. I have a few papers regarding its use in green halogenations, with a side-by-side comparison with tcica, and it tends to produce higher yields. I have seen and can get BCDMH.

I have another paper that talks about its preparation, which reacts trisilver cyanurate with bromine vapor at 150C. Not something I am interested in attempting at this time.

Ag3Cy + 3Br2 -> Br3Cy + 3AgBr

I will look into BCDMH.

[Edited on 10-2-2015 by Loptr]

AvBaeyer - 10-2-2015 at 21:23

Loptr,

I use 1,3-dibromo-5,5-dimethylhydantoin for brominations, for example in place of NBS. There is quite a bit of literature on the use of the compound, much of it free access, if you search on Google. I have used it for ketone bromination and both bromine atoms are available to react.

The 1,3-dibromo-5,5-dimethylhydantoin can be found online as a non-chlorine sanitizing agent. The one I found was Brilliance Spa Sanitzer. (http://www.amazon.com/Brilliance-Bromine-Sanitizer-Spas-Poun...) I cannot take credit for finding this compound as someone else here mentioned it sometime ago.

AvB

AvBaeyer - 10-2-2015 at 21:32

I forgot to add this in case you want TBCA. The attached paper says that TBCA is a stable solid that can be easily synthesized from isocyanuric acid and NaBr in the presence of oxone and give references. Isocyanuric acid can be obtained from TCCA and oxone is easily available from pool chemical suppliers - again on Amazon.

AvB

Attachment: TBCA mediated microwave-assisted Hofmann rearrangement[1].pdf (174kB)
This file has been downloaded 693 times

CuReUS - 10-2-2015 at 21:35

Quote: Originally posted by AvBaeyer  
oxone is easily available from pool chemical suppliers
AvB

I thought oxone was just another name for TCCA:o .Is oxone similar to bleach?I know its structurally diferent:P,but is it similar chemically ?

[Edited on 11-2-2015 by CuReUS]

woelen - 10-2-2015 at 23:54

Oxone is a triple salt, which can be written as KHSO4·K2SO4·2KHSO5.
The HSO5(-) ion is the active ion, it contains the monopersulfate group.
The simple salts K2SO5 and KHSO5 are not stable and lose oxygen very quickly, but the triple salt, sold as 'oxone' is stable and can be kept for years without decomposition as long as it is kept dry.

Oxone is used as a halogen-free replacement for swimming-pool treatment. It is more expensive, but for people who get irritated eyes or skin from chlorine or bromine-based pool treatment, oxone is a good alternative.

[Edited on 11-2-15 by woelen]

Loptr - 11-2-2015 at 07:45

Quote: Originally posted by AvBaeyer  
I forgot to add this in case you want TBCA. The attached paper says that TBCA is a stable solid that can be easily synthesized from isocyanuric acid and NaBr in the presence of oxone and give references. Isocyanuric acid can be obtained from TCCA and oxone is easily available from pool chemical suppliers - again on Amazon.

AvB


Thank you, AvB!

I figured that TCCA could be used to prepare TBCA but hadn't found a procedure.

Loptr - 11-2-2015 at 19:41

Quote: Originally posted by CuReUS  
Quote: Originally posted by AvBaeyer  
oxone is easily available from pool chemical suppliers
AvB

I thought oxone was just another name for TCCA:o .Is oxone similar to bleach?I know its structurally diferent:P,but is it similar chemically ?

[Edited on 11-2-2015 by CuReUS]


I think I purchased my oxone here.
http://www.mkmpoolspa.com/robarb-ultra-quick-swim-2-2-lb/